Patent EP-0649839-A1 (EP)
Inventor: PILL THOMAS DIPL CHEM DR RER N
IPC: C07D239/95
Filed: 1994-10-04
Abstract: The invention relates to heterocyclic carbamates of the formula (I)
       
 in which
     a) 
X denotes the group CR⁴ and Y denotes the group CR⁵, where 
R¹ stands for a C₁- to C₆- lower alkyl radical, for a substituted C₁- to C₆- lower alkyl radical, for an aryl-C₁- to C₆- lower alkyl radical, for an aryl radical or for a heterocyclic radical, 
R² and R³ independently of one another stand for radicals of the following meaning: 
hydrogen atoms, C₁- to C₆- lower alkyl radicals, C₁- to C₆- lower alkoxy radicals, C₁- to C₆- lower alkylthio radicals, halogen atoms, nitro groups, hydroxyl groups, trifluoromethyl radicals, cyano radicals, sulpho radicals, C₁- to C₆- lower alkylsulphonyl groups, carboxylic acid groups, C₁- to C₆- lower alkoxycarbonyl radicals, C₁- to C₆- lower alkoxycarbonyloxy radicals, acetamido radicals, benzamido radicals or the group -N(R⁶)R⁷, 
R⁴ and R⁵ independently of one another stand for a hydrogen atom, for a C₁- to C₆- lower alkyl radical, for a substituted C₁- to C₆- lower alkyl radical, for an aryl-C₁- to C₆- lower alkyl radical or for an aryl radical, 
m and n independently of one another are equal to 0, 1, 2, 3 or 4, and 
R⁶ and R⁷ independently of one another stand for a hydrogen atom or a C₁- to C₆- lower alkyl radical, 
or in which 
   b) 
X and Y denote a nitrogen atom, where 
m, n, R¹, R², R³, R⁶ and R⁷ have the meanings mentioned under a), 
with the proviso that R¹ is not ethyl and if R¹ denotes a methyl radical, an unsubstituted C₃- to C₆- lower alkyl radical, a phenyl radical or a benzyl radical, at least one radical R² or R³ is different from a hydrogen atom or a halogen atom, 
or in which 
   c) 
X denotes a nitrogen atom and Y denotes the radical CR⁵, where 
R¹ stands for a substituted C₁- to C₆- lower alkyl radical, for an aryl-C₁- to C₆- lower alkyl radical, for an aryl radical or for a heterocyclic radical, 
R⁵ stands for a hydrogen atom or for a C₁- to C₆- lower alkyl radical, and 
m, n, R², R³, R⁶ and R⁷ have the meanings mentioned under a), 
or in which 
   d) 
X denotes a nitrogen atom and Y denotes the radical CR⁵, where 
R⁵ stands for a substituted C₁- to C₆- lower alkyl radical, for an aryl-C₁- to C₆- lower alkyl radical or for an aryl radical, and 
m, n, R¹, R², R³, R⁶ and R⁷ have the meanings mentioned under a), 
or in which 
   e) 
Y denotes a nitrogen atom and X denotes the radical CR⁴, where 
R⁴ stands for a substituted C₁- to C₆- lower alkyl radical or for a radical of the general formula (II) 
 
 
 
        ―Z―R⁸   (II) 
 
 
 
where Z stands for a carbonyl or carboxyl group, a sulphur atom or an oxygen atom and 
R⁸ stands for a C₁- to C₆- lower alkyl radical, for a substituted C₁- to C₆- lower alkyl radical, for an aryl-C₁- to C₆- lower alkyl radical or for an aryl radical, and 
m, n, R¹, R², R³, R⁶ and R⁷ have the meanings mentioned under a), 
or in which 
   f) 
Y denotes a nitrogen atom and X denotes the radical CR⁴, where 
R¹ stands for a substituted C₁- to C₆- lower alkyl radical, for an aryl radical or for a heterocyclic radical, 
R⁴ stands for a hydrogen atom, for a C₁- to C₆- lower alkyl radical, for a substituted C₁- to C₆- lower alkyl radical, for a substituted C₁- to C₆- lower alkyl radical, for an aryl-C₁- to C₆- lower alkyl radical or for an aryl radical, and 
m, n, R², R³, R⁶ and R⁷ have the meanings mentioned under a), 
with the proviso that if R², R³ and R⁴ denote hydrogen atoms, R¹ is different from an unsubsituted phenyl radical, 
and 
their salts with physiologically tolerable acids and bases, 
and their use as antithrombotics and as inhibitors of enzymes breaking down connective tissue, in particular granulocyte elastase.